Self-condensation

Self-condensation is an organic reaction in which a chemical compound containing a carbonyl group acts both as the electrophile and the nucleophile in an aldol condensation. It is also called a symmetrical aldol condensation as opposed to a mixed aldol condensation in which the electrophile and nucleophile are different species.

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For example, two molecules of acetone condense to a single compound mesityl oxide in the presence of an ion exchange resin:^[1]

2 CH₃COCH₃ → (CH₃)₂C=CH(CO)CH₃ + H₂O

For synthetic uses, this is generally an undesirable, but spontaneous and favored side-reaction of mixed aldol condensation, and special precautions are needed to prevent it.

References

1. ^ Ketone Condensations Using Sulfonic Acid Ion Exchange Resin N. Lorette; J. Org. Chem.; 1957; 22(3); 346-347.